Adducts of tetrabromodialkoxy cyclopentadienes and acrylonitrile

ABSTRACT

COMPOSITIONS OF MATTER THAT ARE THE DIELS-ALDER ADDUCTS OF TETRABROMODIALKOXY CYCLOPENTADIENES HAVING THE GENERAL FORMULA C5BR4(OR)2 WHEREIN R IS AN ALKYL RADICAL HAVING FROM 1 TO 8 CARBON ATOMS AND ACRYLONTRILE. SAID ADDUCTS HAVE UTILITY IN PIG WEED CONTROL AGENTS.

United States Patent ADDUCTS OF TETRABROMODTALKGXY CYCLO- PENTADEENES AND ACRYLONITRILE Richard Garth Pews, Midland, Clare R. Hand, Sanford, and Carleton W. Roberts, Midland, Micln, assignors to The Dow Chemical Company, Midland, Mich. N0 Drawing. ()riginal application Apr. 12, 1968, Ser. No. 721,106, new Patent No. 3,489,814, dated Jan. 13, 1970. Divided and this application June 16, 1969, Ser.

Int. Cl. C07c121/48 US. Cl. 260-464 1 Claim a... M... W

ABSTRACT OF THE DISCLOSURE Compositions of matter that are the Diels-Alder adducts of tetrabromodialkoxy cyclopentadienes having the general formula C Br (OR) wherein R is an alkyl radical having from 1 to 8 carbon atoms and acrylonitrile. Said adducts have utility in pig weed control agents.

This application is a divisional application of our prior application Ser. No. 721,106 filed Apr. 12, 1968, now US. Pat. 3,489,814.

This invention concerns new compositions of matter that are the adducts of tetrabromodialkoxy cyclopentadienes and acrylonitrile.

The tetrabromodialkoxy cyclopentadiene starting materials have the general formula Br Br wherein R is an alkyl radical having from 1 t0 8 carbon atoms. The compounds are prepared by reacting hexabromocyclopentadiene with an alkali metal alkoxide at temperatures between about and minus 80 C. and at atmospheric pressure or thereabout. The reaction is illustrated by the equation for the dimethoxy compound as follows:

Other dialkoxy compounds are prepared by employing the corresponding alkali metal alkoxide, e.g., sodium ethoxide, potassium propoxide, sodium butoxide, sodium hexoXide or potassium octoxide, in the reaction with hexar broznocyclopentadiene to form the corresponding derivatives.

The tetrabromodialkoxy cyclopentadienes undergo the Diels-Alder reaction with certain ethylenically unsaturated organic compounds to form other new compositions of matter.

We have found that the tetrabromodialkoxy cyclopentadienes having the above formula react with acrylonitrile to form the corresponding dienophiles.

3,629,315 Patented Dec. 21, 1971 ice EXAMPLE A charge of 10 grams of tetrabromodimethoxycyclopentadiene and 5 m1. of acrylonitrile were sealed in a glass tube and heated under time and temperature conditions as follows: 1 hour at 140 C.; 1 hour at 160 C.; and 1 hour at 190 C. After cooling the product was recovered. There was obtained 6 grams of crystalline product melting at 95-96 C. It was analyzed and found to contain:

Theory C I-l Br O N '(percent): C, 24.24; H, 1.83; Br, 64.64. Found (percent): C, 24.30; H, 1.78; Br, 64.85.

The compound has the structure BrC /OCH3 CHC:N 3O O BrC 1 Gem CH2 C Br In tests of the compound as the active ingredient in spray compositions for control of pig weed it was found to give 100 percent kill at a concentration of 10 parts per million parts of the spray composition.

We claim:

1. An adduct of 1,2,3,4-tetrabromo-5,S-dimethoxycyclopentad'iene and acrylonitrile of the formula Br CH2 References Cited UNITED STATES PATENTS 3,515,740 6/ 1970 Frampton 260-464 JOSEPH PAUL BRUST, Primary Examiner US Cl. X.R. 71--105 

